(3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene

Base Information

• Chemical Name: (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene
• CAS No.: 214753-16-9
• Molecular Formula: C₁₇H₂₅NO₄
• Molecular Weight: 307.39
• Mol file: 214753-16-9.mol

Synonyms:(3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene

Chemical Property of (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene

There total 1 articles about (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

2-bromoallyl alcohol (598-19-6) + N-carbobenzoxy-L-leucinal (70853-26-8,86852-22-4,71413-15-5) → (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene (214753-16-9)

Guidance literature:

2-bromoallyl alcohol; With tert.-butyl lithium; In diethyl ether; at -78 - 0 ℃; for 4h;

N-carbobenzoxy-L-leucinal; In diethyl ether; at -78 - 0 ℃; for 3.5h;

DOI:10.1016/S0968-0896(98)00089-3

Reference yield: 80.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene (214753-16-9) → (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene (214753-68-1)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0968-0896(98)00089-3

Reference yield:

(3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene (214753-16-9) → (2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane (214753-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / imidazole / tetrahydrofuran / 12 h / 20 °C

2: 93 percent / (ClCO)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

3: H₂O₂; i-Pr₂NEt / benzonitrile / 15 h / 0 - 4 °C

4: 97 percent / H₂ / Pd-c / methanol

5: 75 percent / i-Pr₂NEt; HATU / CH₂Cl₂ / 8 h / 20 °C

With 1H-imidazole; oxalyl dichloride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; benzonitrile; 1: Substitution / 2: Swern oxidation / 3: Epoxidation / 4: Hydrogenolysis / 5: Substitution;

DOI:10.1016/S0968-0896(98)00089-3

upstream raw materials:

2-bromoallyl alcohol

N-carbobenzoxy-L-leucinal

Downstream raw materials:

(3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene

(4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1-heptene

(2R,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1,2-oxiranylheptane

(2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane